1: ammonium cerium (IV) nitrate; pyridine-2,6-dicarboxylic acid / water; acetonitrile / 0.5 h / 0 °C 2: sodium dithionite / water; dichloromethane / 1 h / 20 °C 3: phosphorous pentoxide / dichloromethane / 6 h / 20 °C 4: potassium tert-butylate / tetrahydrofuran / 1.5 h / -20 °C 5: Pd(1,2-bis(diphenylphosphino)ethane)Cl2; lithium triethylborohydride / tetrahydrofuran / 2 h / 20 °C 6: anhydrous iron chloride; hydrogenchloride / ethanol; water; hexane / 3 h / 20 °C View Scheme

anhydrous iron chloride in dichloromethane T=40°C; Friedel-Crafts Alkylation; 8 h; Overall yield = 67 percent; Overall yield = 1.16 g;

montmollironite K-10 in neat (no solvent) T=80°C; Friedel-Crafts Alkylation; 16 h; Time; stereoselective reaction;

1: copper dichloride; triethyl amine hydrochloride / acetonitrile / 8 h / 80 °C 2: anhydrous iron chloride / dichloromethane / 8 h / 40 °C View Scheme

1: copper dichloride; triethyl amine hydrochloride / acetonitrile / 8 h / 80 °C 2: anhydrous iron chloride / dichloromethane / 8 h / 40 °C View Scheme

tin(IV) chloride in 1,2-dichloro-ethane T=80°C; Friedel-Crafts reaction; 8 h; Product distribution; Further Variations:ReagentsSolventsTemperaturesreaction times;

tin(IV) chloride in 1,2-dichloro-ethane T=80°C; Friedel-Crafts reaction; 8 h; Product distribution; Further Variations:ReagentsSolventsTemperaturesreaction times;

magnesium; copper(I) bromide 1.) THF, 2.) THF, 0 deg C, 2h; Yield given. Multistep reaction;